The role of Jacques was supposed to be played by Jean-Claude Van Damme up until a week before shooting began. Gunn said "the guy was kind of A.W.O.L. I just couldn't risk that personality type on this movie." Kevin Bacon stepped in as a last minute replacement.
Rainn Wilson came to the project via Jenna Fischer's relationship with her ex-husband James Gunn. Gunn was discussing his script with Fischer and asked her to take a look at it, sending her a copy on the set of The Office (2005). Fischer read the script, loved it and thought Wilson would be a great choice as the lead. She gave the script to her co-worker, and Wilson immediately decided to make the film.
Towards the end of the movie, when Liv Tyler is in her rehab group session, she is heard stating "f**ked up, insecure, neurotic, and emotional". This is a reference and nod to her rocker father Steven Tyler (of Aerosmith) and his 1980's song "FINE" which is an acronym for the same line.
As this was a low budget independent production, everyone was paid scale.
James Gunn wanted John C. Reilly to star, but he wasn't thought to be a big enough name. Gunn and Reilly would end up working together in Guardians of the Galaxy (2014).